CN113773342A - Gemini surfactant connected by organosilicon group and preparation method and application thereof - Google Patents
Gemini surfactant connected by organosilicon group and preparation method and application thereof Download PDFInfo
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- CN113773342A CN113773342A CN202111068431.8A CN202111068431A CN113773342A CN 113773342 A CN113773342 A CN 113773342A CN 202111068431 A CN202111068431 A CN 202111068431A CN 113773342 A CN113773342 A CN 113773342A
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- gemini surfactant
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 100
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000003921 oil Substances 0.000 claims abstract description 28
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- -1 alkyl carboxylic acid Chemical class 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 22
- 229920002545 silicone oil Polymers 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 150000003141 primary amines Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 6
- 239000012267 brine Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 5
- 239000003760 tallow Substances 0.000 claims description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 5
- 239000004970 Chain extender Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- VJJJVFXZIZLJRT-UHFFFAOYSA-N diphenyl(disilyloxy)silane Chemical compound C1(=CC=CC=C1)[Si](O[SiH3])(O[SiH3])C1=CC=CC=C1 VJJJVFXZIZLJRT-UHFFFAOYSA-N 0.000 claims description 3
- REPWJCMYAKEVRF-UHFFFAOYSA-N phenyl(silyloxysilyloxy)silane Chemical compound [SiH3]O[SiH2]O[SiH2]C1=CC=CC=C1 REPWJCMYAKEVRF-UHFFFAOYSA-N 0.000 claims description 3
- 238000007142 ring opening reaction Methods 0.000 claims description 3
- BVIXLMYIFZGRBH-UHFFFAOYSA-M sodium;2-chloroethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCl BVIXLMYIFZGRBH-UHFFFAOYSA-M 0.000 claims description 3
- TZLNJNUWVOGZJU-UHFFFAOYSA-M sodium;3-chloro-2-hydroxypropane-1-sulfonate Chemical compound [Na+].ClCC(O)CS([O-])(=O)=O TZLNJNUWVOGZJU-UHFFFAOYSA-M 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- FVRSVYZRCZZKJT-UHFFFAOYSA-N OOS(=O)(=O)CCC.[Na] Chemical compound OOS(=O)(=O)CCC.[Na] FVRSVYZRCZZKJT-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 230000033558 biomineral tissue development Effects 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- SESSOVUNEZQNBV-UHFFFAOYSA-M sodium;2-bromoacetate Chemical compound [Na+].[O-]C(=O)CBr SESSOVUNEZQNBV-UHFFFAOYSA-M 0.000 claims description 2
- HNFOAHXBHLWKNF-UHFFFAOYSA-M sodium;2-bromoethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCBr HNFOAHXBHLWKNF-UHFFFAOYSA-M 0.000 claims description 2
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 abstract description 17
- 239000010703 silicon Substances 0.000 abstract description 17
- 238000006073 displacement reaction Methods 0.000 abstract description 9
- 239000000693 micelle Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract description 3
- 239000010985 leather Substances 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 3
- 239000004753 textile Substances 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 14
- 239000000523 sample Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001165 hydrophobic group Chemical group 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000009671 shengli Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012496 blank sample Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0889—Reactions not involving the Si atom of the Si-O-Si sequence
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Silicon Polymers (AREA)
Abstract
The invention provides an organosilicon group-connected gemini surfactant, and a preparation method and application thereof. Belongs to the technical field of oil extraction in oil fields. The organosilicon group-linked gemini surfactant provided by the invention has the following structural formula (1):
wherein R is1、R2Represents a saturated or unsaturated hydrocarbon chain from C8 to C20; r3、R4Represents an alkyl carboxylic acid or sulphonate group; r5、R6Represents methyl and/or phenyl; when R is5、R6Both are phenyl or one of them is phenyl, m is 1; when R is5、R6When all are methyl, m is an integer of 0 to 11. The organic silicon group-connected gemini surfactant provided by the invention has the advantages that the product is easy to dissolve in water and not easy to hydrolyze, has good surface tension and interfacial tension performance, is low in critical micelle concentration, can be suitable for oil displacement exploitation of low-permeability oil reservoirs and oil-wet oil reservoirs, and can be applied to the fields of pesticides, leather, textiles, coatings, petrochemical industry, daily chemicals and the like.
Description
Technical Field
The invention relates to a surfactant and a preparation method thereof, in particular to an organosilicon group-connected gemini surfactant and a preparation method and application thereof.
Background
The surfactant for oil displacement used in the field of tertiary oil recovery at present is generally a hydrocarbon surfactant, and the surfactant takes a hydrocarbon chain as a hydrophobic group and improves the recovery ratio mainly by reducing the oil-water interfacial tension, improving the oil washing efficiency and the like. For low permeability reservoirs and oil-wet reservoirs, it is important to reduce the surface tension, reduce the capillary resistance, remove the water-lock effect of the low permeability reservoir, and convert the oil-wet property of the reservoir into water-wet property, so as to further improve the crude oil recovery ratio. Current hydrocarbon surfactants fail to meet the use needs of such reservoirs in reducing surface tension.
The silicone surfactant takes a siloxane chain as a hydrophobic group, has super-spreadability and super-wettability, can effectively reduce surface tension, changes oil reservoir wettability, and has performance advantages for low-permeability oil reservoir and oil-wettability oil reservoir exploitation. At present, the organosilicon surfactant is mainly used as a wetting agent and widely applied to the fields of pesticides, leather, textile, coating, petrochemical industry and daily chemicals. However, most types contain Si-O-C bonds and are easy to hydrolyze due to high price, and particularly, the organosilicon hydrophobic group is only spread on an oil-water interface and cannot enter the interior of crude oil, and the tension of the organosilicon hydrophobic group on the oil-water interface is not as good as that of a hydrocarbon surfactant, so that the organosilicon hydrophobic group is not widely applied to the field of oil displacement.
The gemini surfactant is formed by connecting two common surfactant molecules through a linking group in a chemical bond mode, and has more excellent performance than the traditional surfactant: the composite material is easy to adsorb on a solution interface, and the surface tension is effectively reduced; the micelle is easy to form, and the critical micelle concentration is lower; the product has a low Kraff point and good low-temperature water solubility; the synergistic effect of the composition and other surfactants is good; the silver soap has good calcium soap dispersing performance and strong salt resistance; sixthly, the obtained product has excellent wettability. The gemini surfactant is more suitable for oil displacement of low-permeability oil reservoirs and oil-wet oil reservoirs.
The organic silicon group is introduced into the hydrocarbon surfactant and is used as a connecting group to synthesize the gemini surfactant, so that the gemini surfactant has the advantages of both the gemini surfactant and the organic silicon surfactant, and has better surface and interface properties and better wettability. Gemini silicone surfactants generally have two structural forms: one is that two organosilicon surfactant molecules are connected through a hydrocarbon chain, and the organosilicon surfactant with the structure has excellent surface performance but does not have the advantage of reducing the oil-water interfacial tension; and the other is that two hydrocarbon surfactants are connected through an organic silicon group, and the organic silicon surfactant with the structure can reduce the surface tension and the interfacial tension simultaneously. But at present, the organic silicon surfactant is mainly of a first structure, and the variety of a second structure is very few, so that the organic silicon surfactant is difficult to meet the use requirements of the field of tertiary recovery of an oil field.
Disclosure of Invention
The invention provides an organosilicon group-connected gemini surfactant, a preparation method and application thereof, wherein the surfactant has the performance of reducing surface tension and interfacial tension, has the advantages of lower critical micelle concentration, excellent wettability and the like, effectively avoids the defect that the organosilicon surfactant is easy to hydrolyze, is suitable for high-temperature high-salinity low-permeability oil reservoirs and oil-wet oil reservoirs, and greatly improves the oil extraction effect.
In order to solve the technical problem, the invention provides an organosilicon group-linked gemini surfactant, which is characterized by having the following structural formula (1):
wherein R is1、R2Represents a saturated or unsaturated hydrocarbon chain from C8 to C20; r3、R4Represents an alkyl carboxylic acid or sulphonate group; r5、R6Represents methyl and/or phenyl; when R is5、R6Both are phenyl or one of them is phenyl, m is 1; when R is5、R6When all are methyl, m is an integer of 0 to 11. It will be appreciated that in the above scheme, when R is5、R6When all are methyl groups, m may be specifically 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
Preferably, R1、R2At least one selected from linear alkyl, coco, tallow and rosin with C8-C20 carbon chain length; r3、R4At least one selected from sodium acetate, sodium ethyl sulfonate and sodium hydroxy propyl sulfonate.
The invention also provides a preparation method of the organic silicon group-connected gemini surfactant according to any one technical scheme, which is prepared by adopting ring-opening reaction of organic primary amine and double-end epoxy silicone oil and then reacting with halogenated alkyl carboxylate or halogenated alkyl sulfonate.
Preferably, the method comprises the following steps:
adding 800mL of organic primary amine and organic solvent of 360-plus-one into a three-port reaction container, stirring and heating to 50-70 ℃, slowly dropwise adding 0.5-0.55mol of double-end epoxy silicone oil, dropwise adding for 2-4h, and continuing stirring and reacting for 2-4h to obtain a gemini surfactant intermediate product connected with an organic silicon group;
adding 0.01mol of phase transfer catalyst cetyl trimethyl ammonium bromide into the intermediate product, adding 1.2-1.5mol of halogenated alkyl carboxylic acid or sulfonate, stirring for 3-5h at 60-80 ℃, dropwise adding alkali solution in the reaction process to adjust the pH value to 8-10, continuing to react for 2-4h after dropwise adding is finished, cooling to normal temperature, adjusting the pH value to be neutral by using hydrochloric acid, standing for layering, removing bottom salt and brine, and removing part of organic solvent under reduced pressure to obtain the dimeric surfactant solution connected with the organosilicon groups.
Preferably, the epoxy-terminated silicone oil is at least one selected from an epoxy-terminated silicone oil capping agent or chain extender with a polymerization degree of 2-10, epoxy-terminated phenyl trisiloxane and epoxy-terminated diphenyl trisiloxane, and has the following structural formula (2):
wherein R is5、R6Represents methyl and/or phenyl; when R is5、R6When all are methyl, m is an integer of 0-8; when R is5、R6And m is 1 when both or one of the phenyl groups is phenyl.
It is understood that the double-ended epoxy silicone oil used is derived from a commercially available product of Ezeta Silicone Ltd, Anhui, and can be selected from IOTA-010, 105-1, IOTA-278, IOTA-279, IOTA 105-1000, and the like. It is worth to say that the double-end epoxy silicone oil contains two epoxy bonds, can react with primary amine to introduce polysiloxane groups, and is used as a connecting group to form a gemini structure.
Preferably, the molar ratio of the added organic primary amine to the double-ended epoxy silicone oil is 1: (0.5-0.55), the molar ratio of the added organic primary amine to the halogenated alkyl carboxylic acid or the sulfonate is 1: (1.2-1.5);
the molar ratio of the added alkali to the halogenated alkyl carboxylic acid or the sulfonate is 1:1, and the volume ratio of the added alkali solution to the organic solvent is 1:3-2: 3.
It can be understood that the above scheme defines the primary organic amine and the epoxy-terminated silicone oil, because if the adding amount is less than the molar ratio, the epoxy-terminated silicone oil is excessive, a tertiary amine intermediate is generated, a quaternary ammonium salt byproduct is finally formed, a multi-polymer compound is formed due to excessive linkage, even insoluble matter is formed, and if the adding amount is more than the molar ratio, the primary organic amine is excessive, the linkage is insufficient, the organic amine carboxylate without polysiloxane groups is finally formed, the content of the gemini surfactant of the target product is reduced, and the surface tension performance of the product is influenced; meanwhile, the molar ratio of the halogenated alkyl carboxylic acid or the sulfonate is also limited because if the adding amount is less than the molar ratio, the halogenated alkyl carboxylic acid or the sulfonate is excessive, the multi-hydrophilic quaternary ammonium salt is generated, and if the adding amount is more than the molar ratio, the incomplete reaction, the excess of the gemini secondary amine intermediate, the reduced hydrophilicity and the low content of the target product are caused, and meanwhile, the hydrolysis loss condition of the halogenated alkyl carboxylic acid or the sulfonate is considered; similarly, the molar ratio of base to haloalkylcarboxylic acid or sulfonate is limited because addition below this molar ratio results in incomplete reaction of the haloalkylcarboxylic acid or sulfonate, while addition above this molar ratio results in excessive pH, aggravates hydrolysis of the haloalkylcarboxylic acid or sulfonate, and consumes more hydrochloric acid for neutralization, resulting in excessive by-products; meanwhile, the volume ratio of the alkali liquor to the organic solvent is limited because if the adding amount is lower than the volume ratio, the organic solvent is excessive, and the burden of subsequent treatment such as distillation concentration is increased, and if the adding amount is higher than the volume ratio, the water content of the system is excessive, and impurities such as inorganic salt are dissolved in the impurities, so that the system is not layered and does not precipitate, the impurity content of the system is high, the product performance is reduced, and the subsequent treatment of further purification is quite complicated.
Preferably, the organic primary amine is selected from at least one of linear fatty amine with carbon chain length of C8-C20, cocoamine, tallow amine and rosin amine; the organic solvent is at least one of absolute ethyl alcohol and isopropanol; the alkali is selected from at least one of sodium hydroxide, potassium hydroxide and ammonia water; the halogenated alkyl carboxylic acid or sulfonic acid is selected from at least one of sodium chloroacetate, sodium chloroethyl sulfonate, sodium 3-chloro-2-hydroxypropanesulfonate, sodium bromoacetate and sodium bromoethylsulfonate.
The invention also provides application of the surfactant containing the organic silicon group and used for reducing pressure and increasing injection in the produced water of a certain block of a victory oil field with the total mineralization of 8207mg/L according to any technical scheme.
Preferably, when the surfactant is used, a compound sample of the gemini surfactant and the 6501 surfactant is added, wherein the use concentration of the compound sample is 0.05-0.3%, and the mass percentage of the gemini surfactant to the 6501 surfactant in the compound sample is 1: 4.
Preferably, the interfacial tension of a compounded sample containing the gemini surfactant is as low as 10 under the conditions of 70 ℃ and 5000r/min-3mN/m order of magnitude.
Preferably, the surface tension of the compounded sample containing gemini surfactants is < 28mN/m at 25 ℃.
Compared with the prior art, the invention has the beneficial effects that:
1. the gemini surfactant connected with the organosilicon groups provided by the invention has two types of hydrophobic groups of hydrocarbon and siloxane, a hydrocarbon chain extends into crude oil, and the siloxane groups are spread on an oil-water interface, so that the surface tension and the interface tension can be simultaneously reduced, and the gemini surfactant has the advantages of structure and performance in the aspect of oil displacement.
2. The gemini surfactant connected by the organosilicon groups, provided by the invention, has the advantages that carboxylic acid, sulfonic acid and hydroxyl are strong hydrophilic groups, are easy to dissolve in water, are not turbid, have no precipitate, and are suitable for oil displacement products, and are suitable for the fields of pesticides, leather, textiles, coatings, petrochemical industry, daily chemicals and the like.
3. Compared with a single-chain hydrocarbon surfactant, the organic silicon group-connected gemini surfactant provided by the invention has lower critical micelle concentration, and can obtain better surface and interface activity at lower concentration.
4. The gemini surfactant connected with the organosilicon groups belongs to a symmetrical tertiary amine structure, and the hydrophilic groups are electronegative as a whole, so that the adsorption consumption of the stratum can be reduced.
5. The selected groups do not contain Si-O-C bonds easy to hydrolyze, and the product has the advantages of temperature resistance and hydrolysis resistance due to the protection effect of long-chain hydrocarbon groups on organic silicon groups; and the product does not contain long polyoxyethylene ether or polyoxypropylene ether groups, has no cloud point and can be used at higher temperature.
6. The invention adopts the ring-opening reaction of long-chain organic primary amine and double-end epoxy silicone oil, and then the reaction with sodium chloroacetate and the like to introduce strong hydrophilic groups, and has the advantages of classical and reliable preparation method, easily obtained raw materials, relatively low price, simple synthesis process, mild reaction conditions and easy realization of industrial production.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1: synthesis of bis (dodecyl-N-hydroxypropyl-propoxy) -tetramethyldisiloxane-N-sodium diacetate surfactant
Adding 185.35g (1.0mol) of dodecylamine and 360mL of absolute ethyl alcohol into 2000mL of a reaction container, stirring and heating to 50-70 ℃, slowly dropwise adding 181.3g (0.5mol) of epoxy end sealing agent into the reaction container for 2h, and continuously stirring for 2h after dropwise adding is finished.
And adding 3.64g (0.01mol) of hexadecyl trimethyl ammonium bromide serving as a phase transfer catalyst into the product, adding 140g (1.2mol) of sodium chloroacetate, controlling the reaction temperature to be 60-80 ℃, and stirring for reaction for 3 hours. And (2) dropwise adding 240g of 20% NaOH solution in the reaction process, adjusting the pH value to be 8-10, continuing to react for 2h after dropwise adding is completed, cooling to normal temperature, adjusting the pH value to be neutral by using hydrochloric acid, standing for 2h for layering, removing bottom salt and brine, and removing part of organic solvent under reduced pressure to obtain the organic silicon gemini surfactant solution. Wherein the active ingredient content of the organosilicon gemini surfactant is about 70%.
The epoxy capping agent in this example is according to formula (1) or formula (2), R5、R6Is methyl, and m is 0.
Example 2: synthesis of bis (octadecyl-N-hydroxypropyl-propoxy) -pentamethyl phenyl trisiloxane-N-sodium bisethanesulfonate surfactant
Adding 135g (0.5mol) of octadecylamine and 200mL of isopropanol into a 1000mL reaction container, stirring and heating to 50-70 ℃, slowly dropwise adding 135g (0.263mol) of epoxy phenyl trisiloxane into the reaction container for 3h, and continuously stirring for 2h after dropwise adding is finished.
And adding 1.82g (0.005mol) of phase transfer catalyst cetyl trimethyl ammonium bromide into the product, adding 125g (0.75mol) of sodium chloroethyl sulfonate, controlling the reaction temperature to be 60-80 ℃, and dropwise adding for 4 hours. And (2) dropwise adding 200g of 21% KOH solution in the reaction process, adjusting the pH value to be 8-10, continuing to react for 2h after the dropwise adding is completed, cooling to normal temperature, adjusting the pH value to be neutral by using hydrochloric acid, standing for 2h for layering, removing bottom salt and brine, and removing part of organic solvent under reduced pressure to obtain the organic silicon gemini surfactant solution. Wherein the active ingredient content of the organosilicon gemini surfactant is about 70%.
The epoxyphenyltrisiloxanes in this example are according to formula (1) or formula (2), R5、R6Wherein one is methyl, one is phenyl and m is 1.
Example 3: synthesis of sodium bis (tallow-N-hydroxypropyl-propoxy) -tetramethyldiphenyltrisiloxane-N-dihydroxypropyl sulfonate surfactant
Adding 135g (0.5mol) of tallow amine and 400mL of absolute ethyl alcohol into 2000mL of a reaction container, stirring and heating to 50-70 ℃, slowly dropwise adding 147.5g (0.25mol) of epoxy diphenyl trisiloxane into the reaction container for 5h, and continuously stirring for 2h after dropwise adding is finished.
And adding 1.82g (0.005mol) of hexadecyl trimethyl ammonium bromide serving as a phase transfer catalyst into the product, adding 118g (0.6mol) of sodium 3-chloro-2-hydroxypropanesulfonate, controlling the reaction temperature to be 60-80 ℃, and dropwise adding for 5 hours. 150g of 7% ammonia water solution is dripped in the reaction process, and the pH is adjusted to be between 8 and 10. And (3) continuing to react for 2h after the dropwise addition is finished, cooling to normal temperature, adjusting the pH to be neutral by using hydrochloric acid, standing for 2h for layering, removing bottom salt and brine, and removing part of the organic solvent under reduced pressure to obtain the organic silicon gemini surfactant solution. Wherein the active ingredient content of the organosilicon gemini surfactant is about 70%.
The epoxydiphenyltrisiloxanes in this example are according to formula (1) or formula (2), R5、R6Are all phenyl groups, and m is 1.
Example 4: synthesis of bis (abietyl-N-hydroxypropyl-propoxy) -eicosyl decasiloxane-N-sodium diacetate surfactant
93g (0.5mol) of rosin amine and 250mL of isopropanol are added into a 2000mL reaction container, the temperature is raised to 50-70 ℃ by stirring, 275g (0.275mol) of epoxy silicone oil chain extender is slowly dripped into the reaction container, the dripping time is 3h, and the stirring is continued for 2h after the dripping is finished.
And adding 1.82g (0.005mol) of phase transfer catalyst cetyl trimethyl ammonium bromide into the product, adding 87.5g (0.75mol) of sodium chloroacetate, controlling the reaction temperature to be 60-80 ℃, and dropwise adding for 3 hours. And (3) dropwise adding 150g of 20% NaOH solution in the reaction process, and adjusting the pH value to be 8-10. And (3) continuing to react for 2h after the dropwise addition is finished, cooling to normal temperature, adjusting the pH to be neutral by using hydrochloric acid, standing for 2h for layering, removing bottom salt and brine, and removing part of the organic solvent under reduced pressure to obtain the organic silicon gemini surfactant solution. Wherein the active ingredient content of the organosilicon gemini surfactant is about 70%.
The epoxy silicone oil chain extender in this example had an average molecular weight of 1000 according to formula (1) or formula (2), R5、R6Are both methyl groups, and m is 8.
Performance test-surface tension test
Gemini surfactants (70% content) synthesized in examples 1 to 4 were prepared into a solution of a certain concentration with tap water, and the surface tension thereof was measured with a JYW-200D full-automatic interfacial tensiometer, and the measurement results are shown in Table 1:
table 1 surface tension units for silicone gemini surfactants: mN/m
As can be seen by combining the data in the table 1, the surface tension (0.3%) of the samples 1 to 4 is less than 28mN/m within the range of 0.01 to 0.3%, which is superior to the technical index of less than or equal to 28mN/m of the standard Q/SH 10202252-2019 surfactant technical requirement for lowering blood pressure and increasing injection of the national Petroleum chemical group Shengli Petroleum administration Limited company enterprise. The organic silicon gemini surfactant provided by the invention has higher surface activity at lower concentration, can effectively reduce the surface tension, and can be diluted to 1/10-1/15 of the concentration of a sample for use.
Performance test-interfacial tension test
The organic silicon gemini surfactant solution provided by the invention can be directly used as a surfactant for pressure reduction and injection increase and oil displacement, but the cost factor and the surface performance of the organic silicon gemini surfactant solution are considered, and the organic silicon gemini surfactant solution is preferably compounded for use.
The organosilicon gemini surfactant solution synthesized in the examples 1-4 is compounded with 6501 surfactant (the mass ratio is 1:4), and the compounded samples are numbered according to the sequence of the examples, wherein the organosilicon gemini surfactant solution (70 percent of effective component) accounts for 10 percent, the 6501 surfactant accounts for 40 percent, the methanol accounts for 20 percent, and the balance is water.
Examples 1-4 the 6501 surfactant used was a commercially available conventional cocodiethanolamine composition having a 1:1.5 ratio of coco acid to diethanolamine, and the surfactants capable of being formulated with the present invention are not limited to cocodiethanolamide.
Preparing 0.05-0.3% of compound sample solution by using produced water (total salinity of 8207mg/L) of a certain block of the Shengli oil field, testing the interfacial tension of the compound sample by using dehydrated crude oil of the certain block of the Shengli oil field by using a TX-500C interfacial tension instrument at 70 ℃ and 5000r/min, and testing the surface tension of the compound sample by using a JYW-200D full-automatic interfacial tension instrument at 25 ℃, wherein the reference value of the interfacial tension is less than 0.1mN/m, namely 10 mN/m-2An order of magnitude; the reference value of the surface tension is less than or equal to 28mN/m, and the test result is shown in Table 2:
table 2 interfacial tension and surface tension of silicone gemini surfactant compounded samples
Note: the composition of the blank sample was: 6501 surfactant 50%, methanol 20%, and water in balance.
As can be seen by combining the data in Table 2, the interfacial tension of the organosilicon gemini surfactant compound sample provided by the invention is as low as 10 within the concentration range of 0.05% -0.3%-3The mN/m order of magnitude is superior to the technical index of the interfacial tension (0.3 percent) of 0.1mN/m of the national petrochemical group Shengli Petroleum administration Limited company enterprise standard Q/SH 10202252-2019 surfactant technical requirement for depressurization and augmented injection, and is also superior to the interfacial tension of a blank sample. The surface tension of the compounded sample at a concentration of 0.05% -0.3% is superior to the concentration level of 0.01% -0.05% of the silicone surfactant alone sample of examples 1-4. Therefore, the organosilicon gemini surfactant compounded sample not only effectively reduces the surface tension, but also can obviously reduce the interfacial tension, and greatly improves the interfacial property. Therefore, the organic silicon gemini surfactant and the compound sample provided by the invention not only can realize the effect of reducing pressure and increasing injection, but also can improve the oil displacement efficiency, and the organic silicon gemini surfactant has the advantages of structure and performance in the fields of reducing pressure, increasing injection and oil displacement.
Claims (11)
1. An organosilicon group-linked gemini surfactant characterized by having the following structural formula (1):
wherein R is1、R2Represents a saturated or unsaturated hydrocarbon chain from C8 to C20; r3、R4Represents an alkyl carboxylic acid or sulphonate group; r5、R6Represents methyl and/or phenyl;
when R is5、R6Are the same asPhenyl or when one of them is phenyl, m is 1; when R is5、R6When all are methyl, m is an integer of 0 to 11.
2. The organosilicon group-linked gemini surfactant according to claim 1, wherein R is1、R2At least one selected from linear alkyl, coco, tallow and rosin with C8-C20 carbon chain length; r3、R4At least one selected from sodium acetate, sodium ethyl sulfonate and sodium hydroxy propyl sulfonate.
3. The method for preparing the gemini surfactant linked by the organosilicon radicals as claimed in claim 1, wherein the gemini surfactant is prepared by ring-opening reaction of organic primary amine and epoxy-terminated silicone oil, and then reaction with halogenated alkyl carboxylate or halogenated alkyl sulfonate.
4. The method of claim 3, comprising the steps of:
adding 800mL of organic primary amine and organic solvent of 360-plus-one into a three-port reaction container, stirring and heating to 50-70 ℃, slowly dropwise adding 0.5-0.55mol of double-end epoxy silicone oil, dropwise adding for 2-4h, and continuing stirring and reacting for 2-4h to obtain a gemini surfactant intermediate product connected with an organic silicon group;
adding 0.01mol of phase transfer catalyst cetyl trimethyl ammonium bromide into the intermediate product, adding 1.2-1.5mol of halogenated alkyl carboxylic acid or sulfonate, stirring for 3-5h at 60-80 ℃, dropwise adding an alkali solution in the reaction process to adjust the pH value to 8-10, continuing to react for 2-4h after dropwise adding is finished, cooling to normal temperature, adjusting the pH value to be neutral by using hydrochloric acid, standing for layering, removing bottom salt and brine, and removing part of organic solvent under reduced pressure to obtain the dimeric surfactant solution connected with the organosilicon groups.
5. The preparation method according to claim 4, wherein the epoxy-terminated silicone oil is at least one selected from the group consisting of a capping agent or a chain extender of epoxy-terminated silicone oil having a degree of polymerization of 2 to 10, an epoxy-terminated phenyltrisiloxane, and an epoxy-terminated diphenyltrisiloxane, and has the following structural formula (2):
wherein R is5、R6Represents methyl and/or phenyl; when R is5、R6When all are methyl, m is an integer of 0-8; when R is5、R6And m is 1 when both or one of the phenyl groups is phenyl.
6. The method according to claim 4, wherein the molar ratio of the added organic primary amine to the double-ended epoxy silicone oil is 1: (0.5-0.55), the molar ratio of the added organic primary amine to the halogenated alkyl carboxylic acid or the sulfonate is 1: (1.2-1.5);
the molar ratio of the added alkali to the halogenated alkyl carboxylic acid or the sulfonate is 1:1, and the volume ratio of the added alkali solution to the organic solvent is 1:3-2: 3.
7. The production method according to claim 4, wherein the organic primary amine is at least one selected from the group consisting of linear aliphatic amines having a carbon chain length of C8 to C20, coco amines, tallow amines, and rosin amines; the organic solvent is at least one of absolute ethyl alcohol and isopropanol; the alkali is selected from at least one of sodium hydroxide, potassium hydroxide and ammonia water; the halogenated alkyl carboxylic acid or sulfonic acid is selected from at least one of sodium chloroacetate, sodium chloroethyl sulfonate, sodium 3-chloro-2-hydroxypropanesulfonate, sodium bromoacetate and sodium bromoethylsulfonate.
8. The use of a gemini surfactant according to claim 1 or 2 in produced water of a certain block of a victory oil field with a total mineralization of 8207 mg/L.
9. The application of the composition according to claim 8, wherein a compounded sample of the gemini surfactant and the 6501 surfactant is added in use, wherein the use concentration of the compounded sample is 0.05% -0.3%, and the mass percentage of the gemini surfactant to the 6501 surfactant in the compounded sample is 1: 4.
10. The use according to claim 9, wherein the interfacial tension of the gemini surfactant-containing compounded sample is as low as 10 at 70 ℃ and 5000r/min-3mN/m order of magnitude.
11. Use according to claim 9, characterized in that the surface tension of the gemini surfactant-containing compounded sample is < 28mN/m at 25 ℃.
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| CN106111008A (en) * | 2016-06-23 | 2016-11-16 | 常熟理工学院 | A kind of silicone betaines surfactant and preparation method thereof |
| US20200171334A1 (en) * | 2016-03-18 | 2020-06-04 | Tyco Fire Products Lp | Organosiloxane compounds as active ingredients in fluorine free fire suppression foams |
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| DE10036532A1 (en) * | 2000-07-27 | 2002-02-21 | Ge Bayer Silicones Gmbh & Co | Novel approximatelya,approximatelyc-aminofunctionalized polysiloxanes are useful in cosmetic formulations for skin and hair care, in polishes and as softeners. |
| CN103764725A (en) * | 2011-04-18 | 2014-04-30 | 迈图高新材料有限责任公司 | Functionalized polyorganosiloxanes or silanes for treating lignocellulose materials |
| US20200171334A1 (en) * | 2016-03-18 | 2020-06-04 | Tyco Fire Products Lp | Organosiloxane compounds as active ingredients in fluorine free fire suppression foams |
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